Middlefield Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Middlefield vacation rentals

View from property

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (154 reviews)
"I loved the location and the view!"
United States
Gabrielly
The price is ￥21,489
￥32,035 total
includes taxes & fees
Jun 24 - Jun 25
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
1 bedroom, desk, iron/ironing board, travel crib

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (42 reviews)
"Extremely cozy, comfortable and clean! Really impressed after walking through the door...details of flowers, fruit, water, and coffee and tea. Pleasantly Surprised and would definitely stay again and recommend. Thank you!!"
United States
Kristen B.
The price is ￥18,911
￥36,368 total
includes taxes & fees
May 27 - May 28
1-bedroom cottage with Grove Beach 🏖️ access.
Property grounds

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (16 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (36 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
The price is ￥25,310
￥42,398 total
includes taxes & fees
May 27 - May 28
Walk To Goodspeed Opera House!
Smart TV, fireplace, books, music library

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (31 reviews)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is ￥24,514
￥46,537 total
includes taxes & fees
Jun 22 - Jun 23
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
1 bedroom, desk, iron/ironing board, WiFi

One bedroom in United States of America, New Haven

One bedroom in United States of America, New Haven
Dwight
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay. The accommodations were clean and spacious and communication was quick and helpful. Would definitely come back!"
United States
Rosanne M.
The price is ￥11,939
￥28,812 total
includes taxes & fees
Jun 2 - Jun 3
One bedroom in United States of America, New Haven
Interior

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Manchester Center
10.0 out of 10, Exceptional, (10 reviews)
"Great place"
United States
Jason
The price is ￥20,057
￥32,974 total
includes taxes & fees
May 26 - May 27
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Property grounds

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (2 reviews)
"the place was clean bed was nice"
United States
Jonathan
The price is ￥19,102
￥25,151 total
includes taxes & fees
May 26 - May 27
Humble Abode #2
Exterior

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (9 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is ￥18,783
￥46,114 total
includes taxes & fees
May 26 - May 27
All New 1BR with tons of Charm
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (23 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
The price is ￥28,785
￥59,685 total
includes taxes & fees
May 31 - Jun 1
#24 *Serenity* A Lakefront Cottage Retreat
Dining

2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
The price is ￥14,613
￥38,565 total
includes taxes & fees
May 27 - May 28
2BR Apartment Near Wesleyan 102
Cookware/dishes/utensils

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.6 out of 10, Exceptional, (15 reviews)
"wonderful stay - great apartment and location and communication!"
United States
Anonymous traveler
The price is ￥12,098
￥38,261 total
includes taxes & fees
May 26 - May 27
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
TV

All new 1BR apartment with all the features you are looking for

All new 1BR apartment with all the features you are looking for
Wallingford Center
The price is ￥18,783
￥46,114 total
includes taxes & fees
May 26 - May 27
All new 1BR apartment with all the features you are looking for
Smart TV

Cozy East Haven Home • Near Beach & Yale

Cozy East Haven Home • Near Beach & Yale
Momauguin
10.0 out of 10, Exceptional, (6 reviews)
"Easy check in and was as described. It was perfect for our needs for a place to stay over the holidays."
United States
Danielle D.
Cozy East Haven Home • Near Beach & Yale
Property grounds

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Killingworth
10.0 out of 10, Exceptional, (56 reviews)
"Stayed here for Valentine's weekend with my wife and it was perfect! Gardner and Kathy were great with communication and the cabin itself was beautiful! It had everything we needed for the weekend and the location is close to many nearby attractions. Book your stay at Mapletree Cabin.. you won't regret it! "
United States
Miguel D.
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
1 bedroom, iron/ironing board, WiFi, bed sheets

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ￥18,783
￥46,114 total
includes taxes & fees
Jun 1 - Jun 2
Once the old Schools house now a newly furnished Apartment
TV

All New Private and Cozy in great location

All New Private and Cozy in great location
Wallingford
8.8 out of 10, Excellent, (6 reviews)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
The price is ￥18,783
￥46,114 total
includes taxes & fees
May 26 - May 27
All New Private and Cozy in great location
Exterior

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is ￥20,773
￥50,592 total
includes taxes & fees
May 26 - May 27
Angelica’s safe haven @ west haven
Smart TV

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.4 out of 10, Exceptional, (22 reviews)
"Great place"
United States
John S.
The price is ￥23,718
￥50,357 total
includes taxes & fees
Jun 16 - Jun 17
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Lobby

Spacious Bohemian Nook

Spacious Bohemian Nook
West New Haven
8.4 out of 10, Very Good, (8 reviews)
"The place was incredibly clean. The instructions were clear for entering and locking up. Great experience! Thanks Dylan. "
United States
Andrew P.
The price is ￥17,908
￥39,975 total
includes taxes & fees
May 26 - May 27
Spacious Bohemian Nook
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middlefield Hotel Reviews

Hotel Marcel New Haven, Tapestry Collection By Hilton

Hotel Marcel New Haven, Tapestry Collection By Hilton

10/10 Excellent
"Very clean and modern hotel."
Hongying 1-night trip
Posted 1 hour ago
Hotel Marcel New Haven, Tapestry Collection By Hilton

Find out more about Middlefield

Search for holiday rentals in Middlefield on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlefield using one of the methods below:

  • View our selection of featured holiday rentals in Middlefield
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Look no further and take a look at our great range of rental properties in Middlefield!

Frequently asked questions

Can I find a vacation rental in Middlefield?

Yes, there are vacation rentals in Middlefield close to Lyman Orchards Corn Maze, or you can select a more remote option if you're looking for extra privacy while you relax. Middlefield is known for its golf courses and waterfalls. Make sure you have time to check out the ski areas and restaurants during your trip.

What are some of the best vacation rentals in Middlefield?

Large Charming Historic House close to Beaches: This vacation home rental outside of Middlefield is located near the beach and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Middlefield?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Middlefield stay.

What’s there to see and do in Middlefield?

Lake Beseck Beach and Wadsworth Falls State Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Lyman Orchards and Powder Ridge Mountain Park and Resort.

What’s a vacation rental in Middlefield like?

A vacation rental is a private property you can book for a couple of days or more in Middlefield. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family trips or small group gatherings.